Formaldehyde → HCID 11807514, compound

HRID 2308185Notes

Reaction equation

HRID 2308185 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]=O.O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:8][C:9]([N:11]1[C@@H:12]([CH:13]([CH3:15])[CH3:14])[C:16](=[O:18])[O:17][CH2:19]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 11807514HCID 11807514, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-valine (25.1 g, 0.1 mol) in toluene (500 ml) are added paraformaldehyde (4.0 g) and p-toluene-sulfonic acid monohydrate (1.0 g), and the mixture is refluxed for 30 minutes, during which the generated water is removed with a Dean-Stark apparatus. The reaction solution is washed successively with a 5% aqueous sodium hydrogen carbonate solution and a saturated brine, dried over magnesium sulfate, and the solvent is removed by evaporation under reduced pressure. The residue is recrystallized from toluene to give (4S)-4-isopropyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester (25.0 g, yield: 95%).

Workup

  1. customis removed with a Dean-Stark apparatus
  2. washThe reaction solution is washed successively with a 5% aqueous sodium hydrogen carbonate solution
  3. dry with materiala saturated brine, dried over magnesium sulfate
  4. customthe solvent is removed by evaporation under reduced pressure
  5. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-0f2f992e97ff41429161ef02179e5cc7
Source dataset
uspto-grants-2004_12
Patent number
US06835714B1

Reaction notes

Loading…